QUESTION BANK

CLASS: XII, CHEMISTRY

UNIT 4: HALOALKNAES & HALOARENES

MULTIPLE CHOICE QUESTIONS

METHODS OF PREPARATION & REACTIONS OF HALOALKANES

Sl.No Question:
1. Free radical monochlorination of methane followed by treatment with sodium metal in ether
yields
(a) Ethane
(b) Ethene
(c) Ethyne
(d) Methyl chloride
2. Which of the following molecules is chiral?
(a) Butan-2-ol
(b) Propan-2-ol
(c) 1-chlorobutane
(d) Butanamine
3. In Lucas test, turbidity appears due to
(a) Greater reactivity of tertiary alcohols
(b) Rectivity of primary alcohols at higher temperature
(c) Role of ZnCl2
(d) Non-solubility of resulting haloalkanes

4. Formation of product in dehydrohalogenetion of haloalkanes is guided by

(a) Markovnikovs rule
(b) Saytzeffs Rule
(c) Antimarkovnikovs rule
(d) None of the above
5. How many products can be generated by monochlorination of 2-methylbutane?
(a) 2
(b) 3
(c) 4
(d) 5
6. What is the product when 2-bromopropane is treated with LiAlH4
(a) Propane
(b) 2-methyl propane
(c) Butane
(d) 2-bromobutane
7. What is the product when methyl chloride reacts with a secondary amine?
(a) Methanamine
(b) Secondary amine
(c) Tertiary amine
(d) None of the above

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8. When propene is treated with HBr in presence of peroxide , its an example of
(a) Nucleophilic substitution reaction
(b) Free radical substitution reaction
(c) Free radical addition reaction
(d)Nucleophilic addition reaction
9. IUPAC name of ClCH2C≡CCH2Br is
(a) 1-bromo-4-chlorobut-2-yne
(b) 4-chloro-1-bromobut-2-yne
(c) Bromochlorobutane
(d) None of the above
10. 1-chlorobutane is treated with KI in dry acetone. Name of the reaction is
(a) Swart’s reaction
(b) Wurtz fittig reaction
(c) Finkelstein reaction
(d) Sandmeyers reaction
11. Among the following which one has weakest carbon – halogen bond?
(a) Benzyl bromide
(b) Bromobenzene
(c) Vinyl bromide
(d) Benzyl chloride
12. Which of the following is an example of vic-dihalide?
(A) Dichloromethane
(B) 1,2-dichloroethane
(C) Ethylidene chloride
(D) Allyl chloride
13. Alkyl halides are prepared from alcohols by treating with-
(A)HCl + ZnCl2
(B) Red P + Br2
(C) H2SO4 + KI
(D) All the above
14. Molecules whose mirror image is non-superimposable over them are known as chiral.
Whichof the following moleculesis chiral in nature?
(A) 2-Bromobutane
(B)1-Bromobutane
(C) 2-Bromopropane
(D) 2-Bromopropan-2-ol

15. The Addition of HBr to 2-Pentene gives –

(A) 2-Bromopentane only.
(B) 3-Bromopentane only.
(C) 2-Bromopentane and 3-Bromopentane
(D) 1-Bromopentane and 3-Bromopentane
16. The reaction (CH3)2CHCl + NaI → (CH3)2CHI + NaCl is known as –
(A) Finkelstein’s reaction
(B) Stephen’s reaction
(C) Kolbe’s reaction
(D) Wurtz reaction

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17. When 2-bromobutane reacts with alcoholic KOH, thereaction is called-
(A) halogenation
(B) chlorination
(C) hydrogenation
(D) dehydrohalogenation
18. The reaction R-Br + NaCN → R – CN + NaBr is an example of –
(A) Elimination Reaction
(B) Nucleophilic Substitution
(C) Electrophilic Substitution
(D) Oxidation Reduction
19. Which of the following will have the maximum dipolemoment?
(A) CH3F
(B) CH3Cl
(C) CH3Br
(D) CH3I
20. Identify A
CH3CH2I + AgCN --------‐>A

(A) A = C2H5NC
(B) A= C2H5CN
(C) A = C2H4
(D) A= C3H7CN

21. The Synthesis of Alkyl Fluoride is best accomplished by

(A) Finkelstein reaction
(B) Swarts synthesis
(C) Free radical reaction
(D) Sandmeyer’s reaction

22. Which of the following reactant gives the best method of preparation of alkyl
halides when reacts with alcohol?
(A)Zn/HCl
(B)PCl5
(C)SOCl2/ Pyridine
(D)PCl3

23. A compound that reacts fastest with Lucas Reagent at room temperature is
(A) butan-1-ol
(B) butan-2-ol
(C) 2-methylpropan -1-ol
(D) 2-methylpropan-2-ol.

24. An organic compound A (C4H9Cl) on reaction with Na/diethyl ether gives a hydrocarbon
which on monochlorination gives only one chloro derivative,
then A is
(A) tert-butyl chloride
(B) sec-butyl chloride
(C) isobutyl chloride
(D) n-butyl chloride

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25. The IUPAC name of a secondary optically active alkyl halide having molecular formula
C5H11Br is
(a) 1-bromopentane
(b) 3- bromopentane
(c) 2- bromopentane
(d) 1-bromo -2-methyl propane
26. Which of the following are arranged in decreasing order of dipole moment
(a) CH3Cl, CH3F, CH3Br
(b) CH3Cl, CH3Br, CH3F
(c) CH3Br, CH3Cl, CH3F
(d) CH3Br, CH3F, CH3Cl
27. Identify Z in the following sequence:
. /
C2H4 ⎯ X ⎯⎯⎯⎯⎯ Y ⎯⎯⎯⎯ Z
(a) CH3CH2I
(b) CHI3
(c) CH3CHO
(d) CH2!-CH2I
28 The reagent required to obtain 1-iodobutane from 1-butene is/are
(a) I2 / red P
(b) KI / acetone
(c) HI / organic peroxide
(d) HBr / H2O2& KI / acetone
29 . /
CH3CH2CH2Cl ⎯⎯⎯⎯ B ⎯ C ⎯⎯⎯⎯⎯⎯⎯⎯ D. In the above reaction, D is
(a) 2,2-dimethylbutane
(b) 2,3- dimethyl butane
(c) n-hexane
(d) allyl bromide
30 Identify the end product (C) in the following sequence:
/ . /
C2H5OH ⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯ A ⎯⎯⎯⎯ B ⎯⎯⎯⎯ C
(a) C2H5CH2NH2
(b) CH3CONH2
(c) C2H5COOH
(d) C2H5NH2 + HCOOH
31 Addition of KI accelerates the hydrolysis of primary alkyl halides because
(a) KI is soluble in organic solvents
(b) I- is a strong base.
(c) I- is a weak base and a poor leaving group.
(d) I-is a powerful nucleophile as well as a good leaving group
32 The product of the reaction of Chloroethane with alcoholic KOH will be an
a) Alkane
b) Alkyne
c) Alcohol
d) Alkene
33 Lucas’ reagent is a mixture of
(A) Anhydrous CaCl2 in conc. HCl
(B) Anhydrous ZnCl2 in conc. HNO3
(C) Anhydrous ZnCl2 in conc. HCl
(D) Anhydrous CaCl2 in conc. HNO3

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34 Ethyl alcohol, Isopropyl alcohol and tert-Butyl alcohol are given in three test tubes, and you
are given Lucas’ reagent. How much time will be taken to confirm that which test tube has
which alcohol?
(A) 30 second
(B) 5 to 6 minutes
(C) 30 to 40 minutes

(D) 60 minutes
35 CH3CH2CH = CH2 + HBr (in the presence of a peroxide)  Major PRODUCT “A”.
Product “A” is
(A) 2-Bromobutane
(B) 1-Bromobutane
(C) Butane

(D)1,2-Dibromobutane
36 (CH3)3CBr + alcoholic solution of KOH  Major Product “P”. The IUPAC name of “P” is
(A) 2-Methylpropane-2-ol
(B) tert-Butyl alcohol
(C) 2-Methylprop-2-ene

(D) 2-Methylprop-1-ene
37 Which of the following is correct reactivityorder of alkyl halides towards nucleophilic
substitution reaction, if “R” is same?
(A) R-Br<R-I<R-Cl<R-F
(B) R-I<R-Br<R-Cl<R-F
(C) R-Cl<R-F<R-Br<R-I

(D) R-F<R-Cl<R-Br<R-I
38 Which one is not a nucleophile?
(A) C2H5O─
(B) C2H5+
(C) SCN─
(D) H2O
39 On treating a mixture of two alkyl halides with sodium metal in dry ether, 2-methyl propane
is obtained. The alkyl halides are
(A) Chloromethane and 1-chloropropane

(B) Chloromethane and chloroethane

(C) 2-chloropropane and chloromethane

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 (D)2-chloropropane and chloroethane

40 How many centers of chirality are present in 3-Bromopent-1-ene?

(A) One
(B) Two
(C) Three
(A) Zero
41 Which of the following compounds is vic-dihalide?
(A) Ethylidene chloride
(B) Ethylene dichloride
(C) Vinyl chloride
(E) Benzal chloride.
42

The correct IUPAC name of above compound is

(A) 1-Bromo-2-ethyl-2-methylethane
(B) 1-Bromo-2-ethylpropane
(C) 1-Bromo-2-methylbutane
(D) 2-Methyl-1-bromobutane
43 Which of the following is most reactive towards hydrolysis by aqueous KOH?
(A) (CH3)3CCl
(B) C6H5CH2Cl
(C) C6H5CHClC6H5
(D) C6H5Cl

44 Bromination of Ethane in presence of sunlight is

a) Nucleophilic substitution
b) Electrophilic substitution
c) Free radical substitution
d) Addition reaction
45 Which one of the following is a Gem-dibromide.
(a) CH3CH(Br)CH2(Br)
(b) CH3CBr2CH3
(c) CH2(Br)CH2CH3

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 (d) CH2BrCH2Br

46 How many monosubstituted product would be obtained on free radical halogenation of neo-
pentane?
(a) 2
(b) 1
(c) 3
(d) 4

47 When HCl gas is treated with propene in presence of benzoyl peroxide, it gives
a) 2-chloropropane
b) allyl chloride
c) no reaction
d) n- propyl chloride

48 The correct order of boiling point of the following compounds is

(i) CH3CH2CH2CH2Br (ii) CH3CH2CH2CH(Br)CH3
(iii) (CH3)2CHCH2Br (iv) (CH3)3CBr
(a) (iv)<(iii)<(ii)<(i)
(b) (iv)<(iii)<(i)<(ii)
(c) (iv)<(ii)<(iii)<(i)
(d) (ii)<(iv)<(ii)<(i)

49 The reaction of 2-bromobutane with KOH in presence of ethanol would result in the
formation of:
(a) butan-2-ol
(b) but-1-ene
(c) but-2-ene
(d) both but-1-ene & but-2-ene
50 In which of the following conversions, phosphorus pentachloride is used as the reagent?
(a) H2C=CH2 → CH3CH2Cl
(b) CH3CH2OH → CH3CH2Cl
(c) H3C-O-CH3 → CH3Cl
(d) CH≡CH → CH2=CHCl

51 The reaction of 2-chlorobutane with Mg and dry ether followed by hydrolysis would form:
(a) butan-2-ol
(b) but-1-ene

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 (c) but-2-ene
(d) butane
52 A mixture of methyl chloride and ethyl chloride on treatment with sodium and dry ether
results in the formation of :
(a) ethane only
(b) butane only
(c) propane only
(d) a mixture of all the above

53 The best reagent(s) for the preparation of ethyl fluoride from ethanol is:
(a) HF, anhy ZnCl2
(b) PF3
(c) HCl/anhy ZnCl2 followed by Hg2F2
(d) F2, sunlight
54 In which of the following molecules carbon atom is chiral.

a) (i), (ii), (iii), (iv)

b) (i), (ii)
c) (iii), (iv)
d) (i), (ii) (iii)
55 The catalyst used in the preparation of an alkyl chloride bythe action of dry HCl on an
alcohol is
(a) anhydrous AlCl3 (b) FeCl3
(c) anhydrous ZnCl2 (d) Cu
56 The following compound is

a) Allyl Chloride
b) Vinyl Chloride
c) Benzyl Chloride
d) Aryl Chloride
57 What is the IUPAC name of the following compound?

a) 1-Bromo-3-methylprop
methylprop-2-ene

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21 Page 8 of 13
 b) 3-Bromo-1-methylpropene
c) 1-Bromobut-2-ene
d) 4-Bromobut-2-ene

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 MULTIPLE CHOICE QUESTION-ANSWER
METHODS OF PREPARATION & REACTIONS OF HALOALKANES

1.a 2.a 3.d 4.b 5.c 6.c 7.c 8.c 9.a 10.c
11.a 12.b 13.d 14.a 15.c 16.a 17.d 18.b 19.a 20.a
21.b 22.c 23.d 24.a 25.c 26.c 27.c 28.d 29.c 30.c
31.d 32.d 33.c 34.b 35.b 36.c 37.c 38.b 39.c 40.a
41.b 42.d 43.c 44.c 45.b 46.b 47a 48.a 49.d 50.b
51.d 52.d 53.c 54.d 55.c 56.b 57.d

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 MULTIPLE CHOICE QUESTIONS
NATURE OF C–X BOND, SUBSTITUTION REACTIONS (DIRECTIVE INFLUENCE OF
HALOGEN IN MONOSUBSTITUTED COMPOUNDS ONLY)

Sl.No Question:
1 The most reactive compound towards SN2 reaction among the following is
(a) Ethyl bromide
(b) Tert butyl bromide
(c) Isobutyl bromide
(d) 2-bromobutane
2. Arrange according to reactivity towards SN2 reaction
1-chlorobutane(A), 1-chloro-2,2-dimethylpropane(B), 1-chloro-2-methylbutane(C),
1-chloro-3-methylbutane(D)
(a) A>D>C>B
(b) A>B>C>D
(c) A>C>B>D
(d) D>B>A>C
3 Allylic halides show high reactivity towards
(a) SN1 reactions
(b) SN2 reactions
(c) Addition reactions
(d) None of the above
4. Which is the most reactive towards SN1 reaction
(A) C6H5CH2Cl
(B) C6H5CH(C6H5)Br
(C) C6H5CH(CH3)Br
(D) C6H5C(CH3)(C6H5)
5. SN1 reaction of alkyl halide leads to
(a) Retention of configuration
(b) Racemisaton
(c) Inversion in configuration
(d) None of the above.

6. Which of the following alkyl halides will undergo SN1 reaction most readily?
(a) (CH3)3C – F
(b) (CH3)3C – Cl
(c) (CH3)3C – Br
(d) (CH3)3C – I
7. A SN2 reaction at an asymmetric carbon of a compound always gives
(a) a single isomer
(b) an enantiomer of the substrate.
(c) a product with opposite rotation
(d) a product mixture of diastereomers
8. Which alkyl halide is most reactive towards SN2?
(A) Ethyl chloride
(B) Isopropyl chloride
(C) Ethyl iodide
(D) tert-Butyl iodide

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9. The correct order of reactivity towards an SN2 reaction among the following compounds
is :
(i)CH3CH2CH2CH2Br ,(ii)CH3CH2CH(Br)CH3 , (iii)(CH3)2CHCH2Br ,(iv)(CH3)3CBr
(a) (iv)<(iii)<(ii)<(i)
(b) (iv)<(iii)<(i)<(ii)
(c) (iv)<(ii)<(iii)<(i)
(d) (ii)<(iv)<(ii)<(i)
10. The reaction of an alkyl halide via SN1 pathway results in :
(a) inversion of configuration
(b) retention of configuration
(c) optically active product
(d) racemisation
11. In SN1 reaction, the recemization takes place. It is due to
(a) inversion of configuration
(b) retention of configuration
(c) conversion of configuration
(d) Both (a) and (b)

12. Most reactive halide towards SN1 reactions is

a) n-Butyl chloride
b) sec-Butyl chloride
c) tert-Butyl chloride
d) All alkyl chloride
13. In SN2 reaction substrate undergo ________________ of the configuration.
a) Retention
b) Inversion
c) racemisation
d) None of these
14. SN1 reaction of alkyl halide leads to
(a) Retention of configuration
(b) Racemisaton
(c) Inversion in configuration
(d) None of the above.

15 Which of the following alkyl halides will undergo SN1 reaction most readily?
(a) (CH3)3C – F
(b) (CH3)3C – Cl
(c) (CH3)3C – Br
(d) (CH3)3C – I

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 16 A SN2 reaction at an asymmetric carbon of a compound always gives
(a) a single isomer
(b) an enantiomer of the substrate.
(c) a product with opposite rotation
(d) a product mixture of diastereomers

KEY/ANSWER SHEET
NATURE OF C–X BOND, SUBSTITUTION REACTIONS
(DIRECTIVE INFLUENCE OF HALOGEN IN MONOSUBSTITUTED COMPOUNDS ONLY)

Question Answer
1 a
2 a
3 a
4 d
5 b
6 d
7 a
8 c
9 c
10 d
11 d
12 c
13 b
14 b
15 d
16 a

The questions submitted by the PGTs (Chemistry) of KVs of Bhubaneswar, Guwahati, Kolkata,
Ranchi, Silchar and Tinsukia Regions.
Vetted by:
Mr. Alok Kumar Pandey, PGT (Chemistry), KV Paradip Port, Bhubaneswar Region.
Email: chemalok1734@gmail.com Ph No. 93865975535

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 QUESTION BANK
CLASS: XII, CHEMISTRY
UNIT 4: HALOALKNAES & HALOARENES
MULTIPLE CHOICE QUESTIONS
IUPAC NAME, NATURE OF C-X BOND AND
REACTIVITY TOWARD NUCLEOPHILIC SUBSTITUTION REACTION

Sl.No Question:
1. Which of the following is most reactive towards aqueous NaOH.
(a) C H Cl
(b) C H CH Cl
(c) C H Br
(d) BrC H Br
2. Aryl halides are less reactive towards nucleophilic substitution reactions as compared to
alkyl halides due to
(a) formation of a less stable carbonium ion in aryl halides
(b) resonance stabilization in aryl halides
(c) presence of double bonds in alkyl halides
(d) inductive effect in aryl halides.
3 The main difference between C – X bond of a haloalkane and a haloarene is
(a) C – X bond in haloalkanes is shorter than haloarenes
(b) in haloalenes the C attached to halogen in C – X bond is sp3 hybridised
while in haloarenes it is sp2 hybridised.
(c) C – X bond in haloarenes acquires a double bond character due to higher
electronegativity of X than haloalkanes.
(d) haloalkanes are less reactive than haloarenes due to difficulty in C – X
cleavage in haloalkanes.
4. Arrange the following compounds in increasing order of rate of reaction towards
nucleophilic substitution.
(I) (II) (III)

(a) III < II < I

(b) II < III < I
(c) I < IIII < II
(d) I < II < III

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 5 The reaction of toluene with chlorine in the presence of light yields
(a) (b)

(b) (d)

6 The reaction of toluene with chlorine in the absence of light yields

(a) (b)

(b) (d) Mixture of (b) and (c)

7. Which is the correct IUPAC name for

(a) Methylchlorobenzene
(b) Toluene
(c) 1-Chloro-4-methylbenzene
(d) 1-Methyl-4-chlorobenzene
8. Which of the following compounds do not undergo nucleophilic substitution reactions
easily?
(a) p-chlorotoluene
(b) 3-chloropropene
(c) benzyl chloride
(d) 3-bromopropene

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 9. Which one is most reactive towards reaction?
(a) C H CH Br
(b) C H CH C H Br
(c) C H CH CH Br
(a) C H C CH C H Br
10. Chlorobenzene on treatment with acetyl chloride in presence of anhydrous AlCl3 gives
(a) o-chloroacetophenone
(b) p-chloroacetophenone
(c) o- and p-chloroacetophenone
(d) (d) m-chloroacetophenone

11. p-dichlobezene has higher melting point than its o- and isomers because
(a) p- dichlorobenzene is more polar than o- and m- isomer.
(b) p-isomer has a symmetrical crystalline structure.
(c) boiling point of p- isomer is more than o- & m-isomers
(d) All of these are correct.
12. Chlorobenzene on reaction with NaOH at 300K followed by acidic hydrolysis produces
a) Phenol b) Sodium phenoxide
c) Benzaldehyde d) Benzoic acid
13. The reason for the attack of a nucleophile is difficult on monosubstituted benzene is
I) Negative electron cloud above and below the benzene ring
II) Instability of phenyl cation
III) The electronegativity of Sp2 C atom is more as compared to Sp3 carbon
Select the correct option
a) I only b) I & II both
c) Only III d) I, II, III
14. In Dow’s process, preparation of Phenol becomes faster on applying which of the group
on Benzene?
a) EWG b) EDG
c) Both a and b d) None of the above
15. Electron withdrawing group at ortho and para position increases the rate of reaction of
basic hydrolysis of Chlorobenzene due to
a) It stabilizes the positive charge that comes on the carbon to which EWG is attached
b) It stabilizes the negative charge that comes on the carbon to which EWG is attached
c) It starts a reaction with EWG directly.
d) It starts reaction with EWG through catalyst
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 16. The rate of reaction of Basic hydrolysis of Chlorobenzene followed by acidification is
fastest in
ropchlorobenzene
a) O – Nitropchlorobenzene b) o, p – di-Nitropchlorobenzene
Nitropchlorobenzene
c) m – Nitropchlorobenzene d) Same in all the above
17. The rate of reaction of Basic hydrolysis of Chlorobenzene followed by acidification is
NOT influenced by EWG at
a) Ortho b) Para
c) Meta d) None of the above
18 Arrange the following compounds in increasing order of rate of reaction towards
nucleophilic substitution:

(a) a < b < c (b) a < b < a

(c) a < c < b (d) c < a < b
19 Arrange the following compound in increasing order of rate of reaction towards
nucleophilic substitution.

(a) i< ii < iii (b) i< iii < ii

(c) ii <i< iii (d) iii < ii <i
20 Arrange the compounds in increasing order of rate of reaction towards nucleophilic
substitution.

21 Arrange the following compounds in the increasing order of their densities

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 22 Aryl halides are extremely less reactive towards nucleophilic substitution reactions due
to the following reasons: (i) In haloarenes, the electron pairs on halogen atom are in
conjugation with π-electrons of the ring. (ii) In haloalkane, the carbon atom attached to
halogen is sp3 hybridised while in case of haloarene, the carbon atom attached to
halogen is sp2 -hybridised. (iii) In case of haloarenes, the phenyl cation formed as a
result of self-ionisation will not be stabilised by resonance.
(iii) What is ‘A’ in the following reaction?

23 The polarity of C-X bond in Haloarenes is less than C-X bond in Haloalkanes:
(a) Due to hybridized orbital
(b) Due to hybridized orbital
(c) Haloalkanes are less reactive than haloarenes
(d) Due to double bond character in haloarenes
24 Haloarenes are less reactive towards Nucleophilic substitution reaction due to
(a) Hybridisation of Carbon (b) polarity of C-X bond
(c) Resonance effect (d) All of the above

25 Haloarenes shows reaction mechanism when: -

(a) An electron releasing group is attached to the benzene ring.
(b) An electron withdrawing group is attached to benzene ring.
(c) A stronger Nucleophile approaches haloarenes.
(d) No Haloarenes does not show nucleophilic reaction at all.
26

, out of these two which one has more tendency to show nucleophilic
substitution reaction.
(a) I show more tendency towards nucleophilic substitution reaction.
(b) II will show more tendency towards nucleophilic substitution reaction
(c) Both will show
(d) None of them will show.
27 The halo groups are the only ortho - para directing that aredeactivating groups. This
helps to know
(A) Electrophilic reactions by haloarenes
(B) Nucleophilic substitution reaction
(C) Both A and B
ZIET Bhubaneswar, 06 October 2021 5
 (D)None of these

28 Which of the following derivatives of benzene would undergo hydrolysis most readily with aq.
KOH
Cl Cl
O2N NO 2

NO 2 NO 2
(A) (B)
Cl
Cl
NO2

NO2
N
NO2
(C) (D)H3C CH3

+
29 Cl ONa

NO2 NO2
Dil. NaOH



NO2 NO2
The above transformation proceeds through
(a) Electrophilic-addition
(b) benzyne intermediate
(c) Activated nucleophilic substitution
(d) Oxirane.
30 Chlorobenzene is
(a) Less reactive than benzyl chloride
(b) More reactive than ethyl bromide
(c) Nearly as reactive as methyl chloride
(d) More reactive than isopropyl chloride
31 Following equation illustrates
200  2500 C
C6H5Cl + 2NaOH 
200 atm
 C6H5ONa + NaCl + H2O
(a) Dow’s process
(b) Kolbe’s process
(c) Carbylamine test
(d) Haloform reaction
32. Why is PhO– a weaker nucleophile than RO– formed in Dow’s process:
(A) Due to Resonance
(b) Due to -I effect of Benzene ring
(C) Due to its large size
(D) None of the above
33. Which of the following undergoes Hydrolysis most easily?

ZIET Bhubaneswar, 06 October 2021 6

 34.

(a) -OCH3 (b) -CH3 (c) -NO2 (d) -H

35. The replacement of chlorine of chlorobenzene to give phenol requires drastic conditions, but
the chlorine of 2, 4-dinitrochlorobenzene is readily replaced since,
(a) nitro groups make the aromatic ring electron rich at ortho/para positions
(b) nitro groups withdraw electrons from the meta position of the aromatic ring
(c) nitro groups donate electrons at meta position
(d) nitro groups withdraw electrons from ortho/para positions of the aromatic ring
36. Aryl halides cannot be prepared by the reaction of aryl alcohols with PCl3, PCl5 or SOCl2
because
(a) phenols are highly unstable compounds.
(b) carbon-oxygen bond in phenols has a partial double bond character.
(c) carbon-oxygen bond is non- polar
(d) all of these
37. Haloarenes are less reactive than haloalkanes towards nucleophilic substitution
reactions due to
a)Nucleophile attacks an electron deficient carbon ring centre
b)bond length of C-X is longer in haloarenes
c)bond length of C-X is shorter in haloarenes
d)sp3 hybridised C in haloarenes is more electronegative and hold electron pair of C-x
tightly

Answers of MCQ
1.b 2.b 3.b 4.d 5.a 6.d 7.c 8.a 9.d 10.c
11.b 12.a 13.d 14.a 15.b 16.b 17.c 18.c 19.a 20.d
21.a 22.c 23.b 24.d 25.b 26.b 27.c 28.b 29.c 30.a
31.a 32.a 33.d 34.c 35.d 36.b 37.c

The questions submitted by the PGTs (Chemistry) of KVs of Bhubaneswar, Guwahati,

Kolkata, Ranchi, Silchar and Tinsukia Regions.
Vetted by:
Mr Alok Kumar Pandey, PGT (Chemistry), KV Paradip Port, Bhubaneswar Region.
Email: chemalok1734@gmail.com Ph No. 93865975535

ZIET Bhubaneswar, 06 October 2021 7

 QUESTION BANK
CLASS: XII, CHEMISTRY
UNIT 4: HALOALKNAES & HALOARENES
MULTIPLE CHOICE QUESTIONS
ELECTROPHILIC SUBSTITUTION REACTION AND THEIR TYPES

Sl.No Question:
1. The nature of halogen is to send an incoming electrophile at which of the positions?
a) Ortho b) Para
c) Ortho, Para both d) Meta

2. Chlorobenzene is formed by reaction of chlorine with benzene in presence of AlCl3.

Which of the following species attacks the benzene ring in this reaction?
(a) Cl
(b) Cl
(c) AlCl
(d) AlCl
3 For the nitration of Chlorobenzene which of the following is TRUE
a) It produces two isomers ortho and para
b) Para isomer is more steam volatile
c) Ortho isomer is more steam volatile
d) Para isomer involves intramolecular H bonding
4. The reaction between an alkyl halide and an aryl halide in presence of sodium in dry ether
is
(a) Williamson synthesis
(b) Fittig reaction
(c) Wurtz reaction
(d)Wurtz Fittig reaction
5 Toluene reacts with a chlorine in the presence of iron(III) chloride giving ortho and para
chloro compounds. The reaction is
(a) Electrophilic elimination reaction
(b) Free radical substitution reaction
(c) Electrophilic substitution reaction
(e) Nucleophilic substitution reaction

ZIET Bhubaneswar, 06-10-21 1

 6 The reaction between aryl halides in presence of sodium in dry ether is
(a) Williamson synthesis
(b) Fittig reaction
(c) Wurtz reaction
Wurtz Fittig reaction
7. The reaction of toluene with Cl2 in presence of FeCl3 gives X and reaction in presence of
light gives Y. Thus, X and Y are
(a) X = benzyl chloride, Y = m-chlorotoluene
(b) X = benzal chloriode, Y = o-chlorotoluene
(c) X = m-chlorotoluene, Y = p-chlorotoluene
(d) X = o- and p-chlorotoluene, Y = benzyl chloride
8. Halogenation of Halobenzene produces
a) o,p - di- Chlorobenzene b) o,m - di-Chlorobenzene
c) o,m,p - tri- Chlorobenzene d) m,p di-Chloropbenzene

9. SN1 reaction of alkyl halide leads to

(a) Retention of configuration
(b) Racemisaton
(c) Inversion in configuration
(d) None of the above.
10. Chlorobenzene on treatment with acetyl chloride in presence of anhydrous AlCl3 gives
(a) o-chloroacetophenone
(b) p-chloroacetophenone
(c) o- and p-chloroacetophenone
(d) m-chloroacetophenone
11. When Chlorobenzene undergoes reaction with sodium forms
a) Naphthalene b) Anthracene
c) p,p’-Dichlorobiphenyl d) Biphenyl
12. Benzene diazonium chloride reacts with hypophosphorous acid to produce:
(a) phenol (b) benzene
(c) p-hydroxyazobenzene (d) benzonitrile
13. Consider the following compound: , , based on the resonance which is
more reactive towards electrophilic reaction:
(A)
(B)
(C) Both
(d) (D) None of these
14. + 2
> > . !" #! $ℎ& & '$#(! &:
280
(A) ,
(B) ,( − (+( (+(,&!-&!&
(C) ,+ − (+( (+(,&!-&!&

ZIET Bhubaneswar, 06-10-21 2

 (D) , 3,4 − 0#, (+( (+(,&!-&!&

15. Order of hydrolysis of the following in increasing order is

Br , Br , Br , (CH3)3CBr

(I) (II) (III) (IV)

(a) I < II < III < IV
(b) I < IV < II < III
(c) IV < III < II < I
(d) I < II < IV < III
16. Which of the following is an example of Sandmeyer reaction?
Cl
FeCl 3
(a) + Cl 2
low temperature
Cl
Cl Cl
uv light
(b) + Cl2 high temperature
Cl Cl
Cl
CH3
CH2Cl
light, high temp.
(c) + Cl2
no. catalyst

+
N NCl Cl

(d) CuCl, heat N2

+
2
17. Predict the order of reactivity of the following compounds in 1 reactions:
, ( ) , ( ) , ( )

(A) ( ) > ( ) > ( ) >

(B) ( ) > ( ) > > ( )
(C) ( ) > > ( ) > ( )
(D) > ( ) > ( ) > ( )
18. Which of the following is INCORRECT about monosubstituted benzenes
a) The existing group decides at which place electrophile goes
b) The electron density is highest at meta position when the existing group is halogen
c) The electron density is highest at ortho and para position when the existing group is
halogen
d) On nitration, Chlorobenzene forms O-Nitrochlorobenzene and p-Nitrochlorobenzene
19. Increasing order of reactivity of following compound toward aromatic electrophic
substitution reaction is

A) Chlorobenzene, B) Anisole, C) Toluene, D) Cyanobenzene

ZIET Bhubaneswar, 06-10-21 3

 a) D < A < C < B

b) B < C < A < D

c) A < B < C < D

d)D < B < A < C

20.

21. When 1-bromo 2,4,6-trinitrobenzene

trinitrobenzene reacts with CH3MgBr to form mainly

(a) 1,3,5-trimethyl--2,4,6-trinitrobenzene

(b) 2,4,6-trinitrotoluene
trinitrotoluene

(c) 1,3,5-trimethyl--2,4,6-trinitrocyclohexane

(d)1,3,5-trinitrobenzene
trinitrobenzene
22. Among the following compounds, the decreasing order of reactivity towards electrophilic
substitution is

(i) (a) < (b) < (c)

(ii) (c) < (b) < (a)

(iii) (a) < (c) < (b)

(iv) (c) < (a) < (b)

23. Which of the following compounds can be classified as aryl halides?

(a) p-ClC6H4CH2CH(CH3)2

(b) p-CH3CHCl(C6H4)CH2CH3

(c) o-BrH2C-C6H4CH(CH3)CH2CH3

(d) C6H5CH2Cl

ZIET Bhubaneswar, 06-10-21

21 4
 24. Which of the following is not an example of electrophilic substitution reaction?

(a) Nitration of chlorobenzene

(b) Sulphonation of chlorobenzene

(c) Reaction of chlorobenzene with NaOH

(d)Reaction of chlorobenzene with CH3Cl in the presence of Lewis acid.

25. The function of anhydrous AlCl3 in the Friedal- Craft reaction is to

(a) Absorb water

(b) Absorb HCl

(c) To produce electrophile

(d)To produce Nucleophile

26. The product of the following reaction will be_________

27. Dipole moment of p-dichloro benzene is zero and that of o-dichloro benzene is 2.54 D.
Because
a) p-dichloro benzene is aryl halide and o-dichloro benzene is alkyl halide
b) p-dichloro benzene is symmetric and o-dichloro benzene is not symmetric
c) o-dichloro benzene is aryl halide and p-dichloro benzene is alkyl halide
d) in p-dichloro benzene the two bond dipoles (C-Cl) cancel out each other while in o-
dichloro benzene this is not possible.
28. Fluorobenzene (C6H5F) can be synthesized in the laboratory
(a) by direct fluorination of benzene with F2 gas
(b) by reacting bromobenzene with NaF solution
(c) by heating phenol with HF and KF
(d) from aniline by diazotisation followed by heating the diazonium salt with HBF4
29. Chlorobenzene reacts with Mg in dry ether to give a compound (A) which further reacts with
ethanol to yield
(a) Phenol (b) Benzene
(c) Ethylbenzene (d) Phenyl ether
30. Benzene reacts with n-propyl chloride in the presence of anhydrous AlCl3 to give
(a) 3 – Propyl – 1 – chlorobenzene (b) n-Propylbenzene
(c) No reaction (d) Isopropylbenzene

ZIET Bhubaneswar, 06-10-21 5

 31. Chlorobenzene can be prepared by reacting aniline with:
(a) hydrochloric acid
(b) cuprous chloride
(c) chlorine in presence of anhydrous aluminum chloride
(d) nitrous acid followed by heating with cuprous chloride
32. On sulphonation of C6H5Cl
(a) benzene sulphonic acid is formed
(b) metachlorobenzene sulphonic acid is formed
(c) orthochlorobenzene sulphonic acid is formed
(d) ortho and para chlorobenzene sulphonic acids are formed
33. With respect to the electrophilic aromatic substitution of chloro-benzene which of the
following is not true
i. A non-aromatic intermediate is formed
ii. Chloro-benzene acts as an electrophile
iii. A proton is lost in the final step
iv. ortho and para product are produced
34. When considering electrophilic aromatic substitution reactions the halides are described
as
i. Ortho/para directing and activating
ii. Ortho/para directing and deactivating
iii. Meta directing and activating
iv. Meta directing and deactivating
35. Which of the following compounds will not give a white precipitate with alcoholic AgNO3
i Bromobenzene
ii 1-Bromopropane
iii. Ethyl bromide
iv. 2-Bromopropane
36. Which of the following compounds will give a white precipitate with alcoholic AgNO3
i Bromobenzene
ii 4-Bromotoluene
iii. Benzyl bromide
iv. 2-Bromotoluene
37. Chlorobenzene is

i)Less reactive than benzyl chloride

ii) More reactive than ethyl bromide

iii) Nearly as reactive as methyl chloride

iv) More reactive than isopropyl chloride

38. If X and Y are C-X bond enthalpies of chlorobenzene and bromo benzene
respectively.What is the relationship between X and Y?
a)X>Y b)X<Y c)X=Y d)X+Y=0
39. Out of the following which has lower dipole moment
a)cyclohexylchloride b)chlorobenzene c)chlorohexane
d) flourobenzene
ZIET Bhubaneswar, 06-10-21 6
 40. The hybridisation of C-X bond in haloarenes is
sp3 b)sp2 c)sp d)sp2d
41. When considering electrophilic aromatic substitution reaction Electron withdrawing
group(nitro) are observed as:
a)o,p directing and activating
b) o,p directing and deactivating
c)m directing and activating
d) m directing and deactivating

42. Chlorobenzene can be prepared by reacting aniline with

a)Hcl b)Cl2/anhy AlCl3 c)CuCl d)HNO2/Cu2Cl2
43. The regent used to convert benzene to bromo benzene is
a)HBr b)Br2/FeBr3 c)Br2/CCl4 d)Br2 in UV light
44. 4-ethylnitrobenzene ----Br2/Uv--?
a)4-(1-bromoethyl)nitrobenzene
b) 4-(2-bromoethyl)nitrobenzene
c)4-ethyl-3-bromonitrobenzene
d) 4-ethyl-5-bromonitrobenzene
45. The conversion of chloro benzene to phenol the reagent used is
a)NaOH b)NaOH/623K,300atm c) NaOH/323K,600atm
d)CH3OH

ANSWER:

1.c 2.b 3.a 4.d 5.c 6.b 7.d 8.a 9.b 10.c
11.d 12.b 13.b 14.a 15.d 16.d 17.a 18.b 19.a 20.a
21.a 22.a 23.a 24.c 25.c 26.b 27.d 28.d 29.b 30.d
31.d 32.d 33.b 34.b 35.a 36.c 37.a 38.a 39.b 40.b
41.c 42.b 43.b 44.a 45.b

The questions submitted by the PGTs (Chemistry) of KVs of Bhubaneswar, Guwahati,

Kolkata, Ranchi, Silchar and Tinsukia Regions.
Vetted by: BHUBANESWAR REGION

ZIET Bhubaneswar, 06-10-21 7